ethyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate synthesis

5synthesis methods

Product Name:ethyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate
CAS Number:1011464-42-8
Molecular formula:C11H15ClN2O2
Molecular Weight:242.7

ethyl 2-tert-butyl-1,6-dihydro-6-oxopyrimidine-5-carboxylate

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ethyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate

1011464-42-8
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Yield:1011464-42-8 95%

Reaction Conditions:

with triethylamine;trichlorophosphate at 40; for 1 h;

Steps:

30.2 Step 2: ethyl 2-(tert-butyl)-4-chloropyrimidine-5-carboxylate

At 0° C., Et₃N (1.1 mL) was added to POCl₃(32 mL), followed by the addition of ethyl 2-tert-butyl-4-hydroxypyrimidine-5-carboxylate (3.70 g, 16.5 mmol). The mixture was stirred at 40° C. for 1 h and the excess POCl₃was removed under vacuum. The residue was carefully poured into ice (400 mL) and was extracted with CH₂Cl₂. The extract was washed with NaHCO₃and water, dried over Na₂SO₄, filtered and concentrated. The crude material was subjected to silica gel column chromatography (10-90% CH₂Cl₂/hexanes) to afford ethyl 2-(tert-butyl)-4-chloropyrimidine-5-carboxylate (3.8 g, 95%) as a liquid. (M+1)⁺=243.4.